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Howard Stern made a lot of enemies. While he built his career on being the edgiest man in terrestrial radio throughout the 1980s and 1990s, earned millions of dollars and even more fans, he also angered a lot of celebrities. Without a doubt, Howard loved to rip on the lifestyles of the rich and famous. He rarely missed a chance to call out the hypocrisy of those in Hollywood. Fans loved him for it. At the time, they were mostly part of the working class and took pleasure in Howard slamming celebrities. Sometimes it was deserved, but other times he got in unnecessary feuds due to being straight-up mean.
Over the last two decades, however, Howard has gone through a massive personal and creative evolution. While he doesn't shy away from slamming a celebrity or two... ahem... ahem... Aaron Rogers and Simon Cowell, he's actually mended quite a few bridges he once burnt. Of course, his move from terrestrial to satellite radio definitely inspired an element of the change. While some of Howard's old fanbase have abandoned him because of this evolution, others love that he's become close with some of the famous people he used to bash...
8 Jon Bon Jovi
Howard and Jon Bon Jovi's relationship started off well enough but as soon as his famous rock band started promoting their work on a rival radio station, Howard started to bash him. In fact, throughout the early 1990s, the two were mortal enemies. Howard felt betrayed and lashed out, causing Jon to do the same. However, the late Sam Kinison bridged the divide and the two became extremely close friends. Not only is Jon a typical guest on The Stern Show, but he even asked Howard to induct him and his band into the Rock and Roll Hall Of Fame.
7 Ellen DeGeneres
One of the reasons part of Howard's old fanbase was so angry with his evolution was because they thought he became what he railed against. In short, Howard became the Hollywood hypocrite he so hated. While these ex-fans may just be bitter that he's not as politically incorrect as he once was, they do make a point when he comes to his relationship with Ellen DeGeneres. In the 1990s and early 2000s, Howard did numerous bits on his show taking down Ellen's sense of humor as well as her "terrible" dancing. Yet, when she appeared on his show years later, he claimed that he "loved" her dancing. Nowadays, the two text back and forth, and Ellen even re-married Howard and his wife Beth on her show.
6 Rosie O'Donnell
Howard called comedian Rosie O'Donnell every nasty word in the dictionary. While he didn't have all that personal of a reason to dislike her, he found her an easy target for his meaner comedy. Because Howard picked on Rosie so much, a couple of his fans started to harass Rosie and even her children. This caused Mia Farrow, a friend of both Howard's and Rosie's to step in and show the two of them that they had more in common than not. Because of that meeting, Howard got to hear Rosie's personal struggles due to his attacks and he promised to stop. A couple of years after he apologized, Rosie went on The Stern Show and the two became fast friends. While Howard claims he feels real shame for being so mean to Rosie, he values the close friendship the two have built.
5 Lena Dunham
"I think he called me 'a fat Jonah Hill-looking girl,'" Lena told Jimmy Fallon during an interview. It's true, Howard was extremely mean to Lena when she first started to become famous. And yet Lena accepted his apology in recent years bringing an end to a notable feud in 2013. Not only did Lena forgive Howard but she also praised him at his birthday show and while speaking to Jimmy Fallon. "I really care about Howard," she said to Jimmy. "I think he's a voice for important causes. I think he's an outspoken feminist." then she said, "I think we should be thankful that he's in the world."
4 Adam Sandler
The origin of Howard Stern and Adam Sandler's feud is based on the radio host's cutting criticism of the SNL alumnus' movies. Howard rarely shied away from pointing out just how bad he felt some of Adam's comedians were. Adam has stated that the criticism weighed heavily on him but accepted Howard's apology in recent years.
"I always felt bad about all the years we didn't speak," Howard said when Adam finally appeared as a guest on his show. "I really did, because I was a total f**king a**h*le." Ever since the two have become very friendly and Adam has returned to the show he vowed never to go on.
3 Bill Maher
Bill Maher got into a lot of flack after comments he made about 9/11. Among many of the people who railed against his opinion of that day was his old friend Howard Stern. Up until that point, Bill was a regular guest on The Stern Show. But then they had a major falling out after Howard slammed Bill's comments on his show. Up until 2019, the two were enemies despite Howard actually liking Bill's HBO show, Real Time. After a party they both attended, Howard apologized for not supporting Bill's right to free speech or allowing him to clarify some of the things he said. This ended their feud and allowed them to become friends again.
2 Sharon Osbourne
Howard was not happy with Sharon Osbourne when she left her hosting duties at America's Got Talent. In fact, he was very outspoken about his issue with his former co-host leaving. This is is because he was extremely close with her and felt abandoned. After a very brief argument, Howard and Sharon rekindled their friendship and have been extremely defensive of one another whenever they've gone through a controversy.
1 David Letterman
Anyone who knows anything about David Letterman knows that he is a recluse. So, he doesn't exactly spend a lot of time with friends. But there's no doubt that he and Howard are exactly that. While Howard was one of David's most regular and iconic guests on The Late Show, they also had a falling out simultaneously. Howard admits to slamming David because he was jealous of him and was subconsciously trying to tear down someone he looked up to. Additionally, Howard made a comment that really upset David's wife. After extensive apologies and a painting Howard made for David's wife, the two comedians mended their broken bridge and have become friends.